Stand-up, sit-down and spontaneity while spending a Chicago Theatre Sunday with Billy Crystal

Few stand-up comedians turned actors/producers/writers/directors have experienced the cultural impact and overall longevity of Billy Crystal, who on his first live tour in eons, instantly sold out the immaculate Chicago Theatre and sparked a second show that filled up nearly as fast. However, the Emmy and Tony Award winner who starred on the small screen in “Soap,” the golden era of “Saturday Night Live,” co-launched “Comic Relief” with Whoopi Goldberg and Robin Williams, is known for mega-movies such as “When Harry Met Sally,” “City Slickers” and “Analyze This,” along with hosting the Oscars nine times could’ve camped out in town all week and still had thousands more stories to tell.

There were so many observations and spontaneous detours that Crystal barely scratched the surface about his most prominent roles until the second half, scanning through all his priceless “SNL” skits, recalling filming “Running Scared” here in town, giving a full play-by-play of the orgasm scene in “When Harry Met Sally” (followed by a screening with Princess Diana) and pitching “City Slickers” to old time Western actor Jack Palance.

Outside of some key anchor points accompanied by video clips, no two shows on “The Spend The Night With Billy Crystal” Tour are the same, thanks in part to moderation from Chicago’s very own Bonnie Hunt (known for her roles in Second City, “Jumanji,” “Jerry Maguire,” “The Green Mile” and much more). Though she served as a highly humorous warm-up act and conversation prompt for the headliner, Crystal had no trouble riffing on just about anything, while also telling behind the scenes stories on much but not quite all of his unreal career.

The nearly two-and-a-half-hour evening began with the New Yorker recalling his kinship with Chicago, where he played places like the now defunct Playboy Club and the Park West long before his days of major fame (let alone being sometimes mistaken for Billy Joel). At 69-years-old, he may bear a slight resemblance to “The Piano Man,” but proved repeatedly he’s a larger than life personality all his own, starting with an early set comparison of having sex back in his younger days to today or taking his one and only acid trip to sidesplitting results.

In actuality, Crystal seems to be quite the family man, avoiding many of the typical Hollywood vices and staying married for 47 years and counting, while currently chasing around his four grandchildren or teaching them classic lines from movies (in spite of getting some concerned calls from school when one of them whipped out some mobster morsels). The Windy City also learned of his professional relationships with several other beloved celebs, including how several comedic portraits led to a lifelong friendship with Muhammad Ali, countless tales about opening for Sammy Davis Jr. in Las Vegas that had everyone in stiches, plus desperately missing Williams.

Despite the Ali segment in particular running about twice as longed as it needed to, the mention of portraying him and Davis did prompt a reflection about political correctness, particularly how Crystal as a white man would likely be frowned upon for wearing black make-up these days. But the comic was quick to point out that he actually knew each of these greats personally and grew up immersed in diversity with his family owning a record store and promoting countless jazz concerts by the likes of Louis Armstrong and Billie Holiday, adding that the current society is too touchy (a comment accompanied by a hearty round of applause).

Outside of a short clip from “Soap,” there was no analysis of being amongst the first to portray an openly gay character on TV, though he did adapt Howard Cosell’s persona as if he was reporting on the current political climate, which was focused mostly on Republicans (not including President Trump), but also touched on Hillary Clinton and Bernie Sanders. In fact, there were so many observations and spontaneous detours that Crystal barely scratched the surface about his most prominent roles until the second half, scanning through all his priceless “SNL” skits, recalling filming “Running Scared” here in town, giving a full play-by-play of the orgasm scene in “When Harry Met Sally” (followed by a screening with Princess Diana) and pitching “City Slickers” to old time Western actor Jack Palance.

Strangely, “Spend The Night…” didn’t mention Crystal and Hunt’s connection of voicing for “Monster’s Inc.,” nor did it have a very concrete ending outside of showing several Academy Awards snippets on the screen, followed by some brief bows and “thank-you’s.” Nonetheless, anyone interested in the entertainer surely scored their fair share of retro tidbits and recent laughs to be satisfied, while leaving the door open for as many of these future engagements as this legendary figure would like to deliver.